Sulphanilamide can be prepared through a multi-step synthesis from acetanilide. First, acetanilide is treated with chlorosulphonic acid to form p-acetamido-benzene-sulphonyl chloride. This intermediate is then reacted with ammonia to form p-acetamido-benzene-sulphonamide. Finally, p-acetamido-benzene-sulphonamide undergoes acid hydrolysis to yield the desired product, sulphanilamide. Sulphanilamide is a white to brown crystalline powder with a melting point of 163-164°C and solubility of 5 g/L in water. It was one of
Principle Synthesis mechanism and identifiacation of sulphanilamide
1. Topic: SULPHANILAMIDE
Subject: Medicinal Chemistry III (Practical)
DEPARTMENT OF PHARAMACEUTICAL SCIENCES
DR. HARISINGH GOUR VISHWAVIDYALAYA
(A Central University), Sagar (MP)
Presented by
KARTIK JATARIYA
B.PHARM
DOPS
5. INTRODUCTION
Sulfanilamide is an organic sulfur compound
structurally similar to p-aminobenzoic acid
(PABA) with antibacterial property. Basically,
it is aniline derivative with sulphonamide
group which is treated as antibacterial drug'.
6. 3D STRUCTURE 2D STRUCTURE
STRUCTURE
4-Aminobenzene sulfonamide
7. BACKGROUND
DISCOVERY
Sulfanilamide was first prepared
in 1908 by the Austrian chemist
Paul Josef Jakob Gelmo (1879–
1961) It was patented in 1909.
HISTORY
In World War II, Soldiers were
used Powdered sulphanilamide to
reduce infection rates and
contributed to a dramatic
reduction in mortality rates
compared to previous wars.
USES
As a antibacterial agent ( wound
infection)
As a antifungal agent (vaginal
yeast infection)
ToXICITY
Alergic reaction/ Liver problems/
Blood problems
8. PRINCIPLE
Sulphanilamide can be prepared by taking
acetanilide and treating it with excess of
chlorosulphonic acid, which gives p-
acetamido-benzene sulphonyl chloride
which readily converted into corresponding
p-acetamido benzene sulphonamide upon
reaction with ammonia or ammonium
carbonate. The acetamido groups can easily
undergo acid catalyzed hydrolysis reaction
toform p-aminobenzene sulphonamide
(Sulphanilamide)"
16. Prepare p-acetamido-benzene-sulphonyl chloride
Place 5 gm of dry acetanilide into a three necked flaskequipped
with a condenser, add 16 ml of chlorosulfonic acid slowly in small
portions.
Shake the flask well and heat theflask on a water bath for 1 hr .
Cool and pour this oily mixtureas a thin stream with stirring into
100 gm of crushed ice.
Rinse with water and broke the ice lumps and stir the mixture for
several minutes.
Filter it at the pump, wash it with cold waterand drain well.
17. Prepare p-acetamido-benzene-sulphonamide
Transfer the crude product obtained above into a round
bottomflask.
Add a mixture of 15ml of ammonia and 15ml of water. Mix the
contents of the flask thoroughly with swirling.
Heat the mixture for 15 mins (below boiling point.). The sulphonyl
chloride is converted into corresponding sulfonamide.
Cool on ice, add dil. sulphuric acid until the mixture was just acidic
to congo red paper.
Collected the product in a buchner funnel
18. Prepare p-amino-benzene-sulphonamide
Transfer the crude product into 500ml flask and add 5ml of
conc. HCl, 10ml of water.
Boil the mixture gently under refluxfor 10-30 minutes.
Cool the mixture to room temperature (should not show any
solid) to this add 3gm of charcoal, heat the mixture to boil.
Place the filtrate in beaker and continuously add 4gm of solid
sodium bicarbonate.
Test the filtrate with litmus paper until neutral. Cool it in ice bath
and filter the precipitate. Recrystallize from water or alcohol.
20. FORMULA – C6H6N2O2S
IDENTIFICATION
On addition of solution of
copper sulphate to a solution of
the alkaline salts of
sulphonilamide, coloured
precipitate or solution obtained.
MOL WEIGHT – 172.2 g /mol
PHYSICAL STATE – White to brown
crystalline powder.
MELTING POINT – 163-164 degree celcius.
SOLUBILITY IN WATER – 5 g/l at 25
degree celcius.
